Amine derivatives of succinic anhydride have been used as emulsifiers.
U.S. Pat. Nos. 5,512,079 and 5,518,517 disclose amine derivatives of succinic acylating agents for use as emulsifiers in delayed release emulsion fertilizers.
Water-in-oil emulsions have been used for a variety of uses including emulsion explosives. Water-in-oil explosive emulsions typically comprise a continuous organic phase and a discontinuous oxidizer phase containing water and an oxygen-supplying source such as ammonium nitrate, the oxidizer phase being dispersed throughout the continuous organic phase. Examples of such water-in-oil explosive emulsions are disclosed, inter alia, in U.S. Pat. Nos. 5,047,175; and 4,828,633. The emulsifier is a salt derived from high molecular weight carboxylic acylating agent coupled to a low molecular weight carboxylic acylating agent. Succinic acids and anhydrides are the preferred acylating agents.
U.S. Pat. No. 4,919,178 discloses water in oil emulsion explosives in which the emulsifier is the reaction product of two components. The first component is the reaction product certain carboxylic acids or anhydrides, including substituted succinic acids and anhydrides with ammonia or an amine and an alkali metal or an alkaline earth metal. The second component is the salt of a phosphorous containing acid.
European Patent application EP 561,600 A discloses a water-in-oil emulsion explosive in which the emulsifier is the reaction product of a substituted succinic acylating agent, having at least 1.3 succinic groups per equivalent weight of substituents, with ammonia and/or an amine. The substituent is a polyalkene having an number average molecular weight of greater than 500 and preferably 1300-1500.
U.S. Pat. No. 4,919,179 discloses a water-in-oil emulsion explosive wherein the emulsifier is a particular type of ester of polyisobutenyl succinic anhydride.
U.S. Pat. No. 4,844,756 discloses a water-in-oil emulsion explosive wherein the emulsifier is a salt produced by reacting a hydrocarbyl substituted carboxylic acid or anhydride, including substituted succinic acids and anhydrides, with ammonia, an amine, and/or an alkali or alkaline earth metal.
U.S. Pat. No. 4,818,309 discloses a water-in-oil emulsion explosive wherein the emulsifier is a polyalkenyl succinic acid or derivative thereof. The succinic acid may be used in the form of an anhydride, an ester, an amide or an imide. A condensate with ethanolamine is preferred.
U.S. Pat. No. 4,708,753 discloses a water-in-oil emulsion suitable for use in explosive and functional fluids wherein the emulsifier is a reaction product of a hydrocarbyl substituted carboxylic acid, including a succinic acid, with an amine. The substituent contains 20-500 carbon atoms, and the aqueous phase contains a water soluble, oil insoluble functional additive.
European Patent EP 102,827 A discloses a water-in-oil emulsion composition useful as a well control fluid. The emulsifier is a polyamine derivative, especially an alkylene polyamine derivative, of a polyisobutenyl succinic anhydride or a borated or carboxylated derivative thereof.
U.S. Pat. No. 4,445,576 discloses a water-in-oil emulsion composition useful as a spacer fluid in well drilling. The emulsifier is an amine derivative, especially a polyamine derivative, of a polyalkenyl succinic anhydride.
U.S. Pat. No. 4,999,062 describes an emulsion explosive composition comprising a discontinuous phase comprising an oxygen-releasing salt, a continuous water-immiscible organic phase and an emulsifier component comprising a condensation product of a primary amine and a poly[alk(en)yl]succinic acid or anhydride and wherein the condensation product comprises at least 70% by weight succinimide product.
United States defensive publication T969,003 discloses water in oil emulsion fertilizer compositions prepared by dissolving an invert emulsifier in an oil such as kerosene. A liquid (aqueous) fertilizer is emulsified with the oil to form an invert emulsifier.
Patent application WO93/16968 discloses a method of transport and storage of fertilizer compositions. The nutrient portion of the fertilizer composition is in the form of the discontinuous water phase of a water in oil emulsion. The emulsifier is added to the oil prior to mixing together the aqueous and oil phases.
Patent application WO96/28436 describes gamma and delta lactones of formulae (I) and (II) ##STR2## used as emulsifiers in explosive compositions comprising a continuous organic phase and a discontinuous aqueous phase containing an oxygen-supplying compound. In the formulae, R is hydrocarbyl, R* is hydrogen, methyl or another hydrocarbyl, and Q is an amide, ammonium salt or ester functionality.
British patent application 0557568A1 discloses fertilizer compositions comprising dispersions or solutions of nutrient supplying fertilizer components and the method for its manufacture. The solution/dispersion constitutes the discontinuous phase of a water in oil emulsion.
B. B. Snider and J. W. van Straten, J. Org. Chem., 44, 3567-3571 (1979) describe certain products prepared by the reaction of methyl glyoxylate with several butenes and cyclohexenes. K. Mikami and M. Shimizu, Chem. Rev., 92, 1021-1050 (1992) describe carbonyl-ene reactions, including glyoxylateene reactions. D. Savostianov (communicated by P. Pascal), C. R. Acad. Sc. Paris, 263, (605-7) (1966) relates to preparation of some .alpha.-hydroxylactones via the action of glyoxylic acid on olefins. M. Kerfanto et. al., C. R. Acad. Sc. Paris, 264, (232-5) (1967) relates to condensation reactions of .alpha.-.alpha.-di-(N-morpholino)-acetic acid and glyoxylic acid with olefins. B. B. Jarvis et al, Synthesis, 1079-82 (1990) relates to reactions of oxocarboxylic acids with olefins under acidic conditions to give .alpha.-hydroxy butyrolactones.
U.S. Pat. Nos. 5,696,060, 5,696,067 and 5,779,742 describe nitrogen containing derivatives of carboxylic acylating agents derived from the reaction product of an amine (C) characterized by the presence within its structure of at least one H--N group and an intermediate formed in the reaction of (A) at least one olefinic compound containing at least one group of the formula ##STR3## and(B) at least one carboxylic reactant selected from the group consisting of compounds of the formula EQU R.sup.3 C(O)(R.sup.4).sub.n C(O)OR.sup.5 (IV)
wherein each of R.sup.3 and R.sup.5 is independently H or a hydrocarbyl group, R.sup.4 is a divalent hydrocarbylene group, and n is 0 or 1, and reactive sources thereof, in amounts ranging from 0.6 moles (B) per mole of (A) to 3 moles (B) per equivalent of (A). In an optional embodiment, the intermediate is prepared by including in the reaction from about 0.5 to about 2 moles, per mole of (B), of (D) at least one aldehyde or ketone. These are describe as useful as performance improving additives for lubricating oil composition.